Cyclohexenone analog bicyclo (condensed ring) compound and its preparation method and uses

A compound and extract technology, applied in the field of cyclohexenone bicyclic new compounds, can solve the problems such as no research reports on anti-tumor activity

Inactive Publication Date: 2006-02-15
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the antitumor activity and active ingredients of Suanzizao jujuba, especially the cyclohexanone bicyclic (fused ring) active compounds involved in the present invention, have not been reported so far.

Method used

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  • Cyclohexenone analog bicyclo (condensed ring) compound and its preparation method and uses
  • Cyclohexenone analog bicyclo (condensed ring) compound and its preparation method and uses
  • Cyclohexenone analog bicyclo (condensed ring) compound and its preparation method and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] The dry bark (3.2kg) of Choerospondias axillaries (Roxb.) Burtt et Hill was crushed and then extracted with 25 liters of ethanol at room temperature for 7 days each time, 4 times in total. The extracts were combined, concentrated and dried to obtain 750 g of ethanol extract. Suspend 750 g of the ethanol extract in 3 liters of water, extract with chloroform, and extract 4 times with 3 liters of chloroform each time. The chloroform extracts were combined and concentrated to dryness to obtain 60 g of extract.

[0055] The obtained extract (60 g) was dry-processed on a vacuum silica gel column (column bed 7.5 cm×18.5 cm), and gradient elution chromatography was performed using petroleum ether-acetone (100:1→2:1) solvent system as the eluent. During the elution process, the polarity of the elution solvent (V P :V A =100:1, 50:1, 10:1, 5:1, etc.). Merge fractions according to TLC detection and activity test results, at V P :V A = 5:1 eluted fraction yielded 10.8 g of ex...

Embodiment 2

[0078] Example 2. Biological activity test

[0079] Experimental samples and experimental methods

[0080] Preparation of the tested sample solution: take the pure compound II isolated and refined in the above Example 1, accurately weigh an appropriate amount, and prepare a solution with the required concentration with methanol for testing the activity.

[0081] Cell lines and cell culture: Mouse breast cancer tsFT210 cell line, human colorectal cancer HCT-15 cell line, human cervical cancer HeLa cell line, human breast cancer MCF-7 cell line, and human ovarian cancer A2780 cell line were used for activity testing.

[0082] Cells were subcultured in RPMI-1640 medium containing 10% FBS at 32°C (tsFT210 cells) or 37°C (HCT-15, HeLa, MCF-7 and A2780 cells) in an incubator filled with 5% carbon dioxide .

[0083] Cell proliferation inhibitory activity test method (Lissamine rhodamine B method or SRB method): human colon cancer HCT-15 cells in logarithmic growth phase, human cerv...

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Abstract

The invention relates to cyclohexenone bicyclo (condensed ring) compound containing one long chain hydrocarbon represented by formula I, extracts containing these compounds, the process for preparing these compounds and extracts and their use (the definitions of R1-R4 in the formula I are disclosed in the specification. The cyclohexenone bicyclo (condensed ring) compounds can be used as cell cycle inhibitors, cell apoptosis inducers, cell propagation inhibitors, and antineoplastic agents.

Description

technical field [0001] The invention relates to a cyclohexenone bicyclic (condensed ring) compound and a preparation method and use thereof. It specifically relates to a cyclohexenone-based bicyclic (fused ring) novel compound containing a long-chain hydrocarbon substituent, an extract containing the compound, a preparation method of the compound and the extract, and a method for preparing cell cycle inhibitors, cell Uses of apoptosis inducers, cell proliferation inhibitors, cancer cell killers and antitumor agents. Background technique [0002] Cyclohexenone bicyclic (fused ring) compounds are mainly composed of a six-membered carbocyclic ring of cyclohexenone and another carbocyclic or heterocyclic ring to form a fused ring, and various substituents are connected to the fused ring skeleton. Among these compounds, there are some reports in the literature that the six-membered carbon ring of cyclohexenone and another saturated five-membered oxygen heterocycle form a fused r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/79C07D307/82A61K31/343A61P35/00
Inventor 崔承彬李长伟蔡兵韩冰
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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